Poeatiojst of dbiawabe



. methyl-3-chlor-benzene,- 1.6 cc. of hydro- Patented May 26, 1931 omen WILHEIJH FITZKY AND ERR/VIN THOHEA, OF FRAN'KFORT-ON-THE-IVIAIN-HOCHST, GER- MANY, ASSIGI-IORS TO GENERAL ANILZNE WORKS, 1110., OF NEW YORK, N. Y., A COR- 7 POlEl-ATION OF DELAWARE AZO-DYESTUFFS ILNSOL'UBLE IN WATER 7 No Drawing. Application filed April 17, 1930, set

. beans wherein R stands for an aromationucleous which is free from any group which would render the dyestufi water-soluble, R is 1ntended to represent especially phenyl nuclei which are free from carboxylic or sulfonic acid groups and may be substituted by such groups as chlorine or methyl. Our dye-studs are obtainable by coupling a 2.3-hydroxynaphthoyl-Q-amino-5-halogen-hydroquinonewhich is free from any dyestulf water-soluble.

The new dyestuffs show better properties of fastness especially to light'than those pregroup rendering the pared from 2-hydroxy-8-naphthoylaminohydroquinone-diinethylether described in U. S. PatentNo. 1,457,114. Some of thenew dyestuffs produced by'our presentinvention are also distinguished by a considerable fastness to bucking.

The following examples illustrate the invention, but they arenot intended. to limit it thereto:

1. lVell boiled and dried-cotton yarnis impregnated with a'solution containing per liter 5 grams of 2.3-hydroxynaphthoyl-Q-amino- 5-chloro-hydroquinone-diethylether, 10 cc. of Turkey red oil of 50% strength and 2000. of

caustic soda solution of 40% strength. The

yarn thus treated is well wrung out and developed with a diazo solution prepared as follows: I I

To 2 grams of hydrochloride of l-amino-Z- chloric acid of 35% strength, and 0.7 2 gram ial No. 445,195, and in Germany February 18, 1929.

of sodium nitrite there are added 2 grams of sodium acetate and the whole is made up with water to 1 liter. 'The material is then rinsed and soaped boiling hot. In this manner a yellowish red of very good fastness to light and to boiling lye is obtained. The dyestufi"; has theprobable following constitution:

been 2. By developing tliecotton yarn impregnated as described in Example 1 with a diazo solution prepared frorn l fi grain of 2.5-dichloraniline, there is obtained an orange brown dyeing of very good fas'tness to light and to boiling lye. "The dyestuifthus produced has the following probable constitution:

" diethylether with adiazotized aromatic base;

OO.NH- -o1 if O z t 3. By using a diazo solution of 2 grams of hydrochloride of 1-am1no-2-methyl-5-chloro bensene; there is obtained yellowish red dyeing of very good fastness to light and to bolllng lye. The dyestui fthus produced has the following probable constitution:

4. By using a diazo solution prepared from lye. The dyestuff has the following probable constitution OH CO.NH C1 CzHs 5. By using a diazo solution prepared from 1.7 gram of l-amino-3anethyl-t.G-dichlorobenzene there is obtained a brown-red dyeing of vary good fastness to light and to boiling lye. lhe dyestuffs have the following probable constitution:

6. By using l-amino-3.5-dimethyl-4-chlorobenzene as diam-component there is obtained on the fiber a Turkey red dyeing of excellent fastness to light and very good fastness to bucking.

7. By using 1-amino-3.5-dimethyl-2-chlorobenzene as diazo-component there is obtained a bluish red dyeing of excellent fastness to light.

8. By using l-amino-2.5-diinethoXy-4-chlorobenzene as diazocomponent there is obtained a bordeaux red dyeing of excellent fastness to light.

9. By using 1-amino-2.l-dimethoxy-5-chlorobenzene as diam-component there is obtained a bordeaux red dyeing of extraordinary fastness to light.

10. 142 parts by weight of 1-amino-2- methyl-5-chlorobenzene are diazotized in the usual manner and the diazo solution is combined with a solution of 40.5 parts by weight of 2 -hydroxy 3 naphthoyl -2 amino 5 chloro-lA-diethoxybenzene in a dilute caustic soda solution, rinsed with Turkey red oil and an amount of sodium acetate sufiicient for binding the excess of the mineral acid. The precipitated dyestuif is filtered 0E and well washed. It corresponds to the formula:

N O C 115 CH H CO.NH Cl CgHs The expression free from any group capable of rendering the dyestufi water-soluble is meant to exclude such groups as, for instance, the sulfonic acid or carboxylic acid group. By the term aromatic nucleus in claim 1, we mean aromatic nuclei of the benzene and napthalene series.

We claim:

1. As new compounds, the azo dyestuffs of the following constitution:

on CO.NH- Hal 1 0 .NHQ-Hal wherein R stands for a phenyl nucleus which is free from any group capable of rendering the dyestuif water-soluble which compounds are when dry colored powders, insoluble in water, yielding when mixed with substrata valuable color lakes and when prepared on the fiber dyeings and printings of very good fastness properties, especially to light.

3. As new compounds, the azo dyestuffs of the fOllOWiIlg constitution:

wherein X stands for hydrogen or a methyl group and 01 represents 1 or 2 atoms of chlorine which compounds are when dry colored. powders, insoluble in Water, yielding when mixed with substrata valuable color lakes and when prepared on the fiber dyeings and printings of very good fastness properties, especially to light.

' Very 4. As new compounds, the azo dyestufi's of the following constitution:

U X hi wherein X stands for hydrogen or a methyl group which compounds are when dry colored powders, insoluble in water, yielding when mixed with substrata valuable color lakes and when prepared on the fiber orangebrown to brick-red dyeings and printings of good fastness properties, especially to H .boirri- 7 01 light.

5. As a new compound, the azo dyestufi of the following constitution:

N: Cl i said compound being when dry a colored powder, insoluble in water, yielding when mixed with substrata valuable color lakes and when prepared on the fiber orangebrown dyeings and printings of very good fastness properties especially to light.

In testimony whereof, we afiix our signatures.

WILHELM FITZKY. ERWIN- THOMA. 

